3-Aminobenzoic Acid → HCID 21569621, compound

HRID 1579855Notes

Reaction equation

HRID 1579855 reaction equation
[CH2:1]([CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=O.[NH2:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=1)[C:25]([OH:27])=[O:26]>C(O)(=O)C>[C:25]([C:24]1[CH:23]=[C:22]([N:21]2[C:11]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[CH2:18][CH2:19][C:10]=3[CH:1]=[C:2]2[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:30]=[CH:29][CH:28]=1)([OH:27])=[O:26]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 122703462-phenacyl-1-tetralone

Product 1

HCID 21569621HCID 21569621, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10.5 g. (0.04 mole) of 2-phenacyl-1-tetralone (m.p. 73°-76°), 5.5 g. (0.04 mole) of m-aminobenzoic acid, and 35 ml. of glacial acetic acid was heated under reflux for 31/2 hours, cooled and filtered. The filter cake was washed with water and dried to provide 8.6 g. of solid, m.p. 225°-228°. Recrystallization from ethanol and from ethanol-water gave off-white crystals, m.p. 253.5°-255°.

Workup

  1. temperatureunder reflux for 31/2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe filter cake was washed with water
  5. customdried
  6. customto provide 8.6 g
  7. customRecrystallization from ethanol
  8. customfrom ethanol-water gave off-white crystals, m.p. 253.5°-255°

Sources & evidence

ORD record
ord-718afd862a22445890df7db2324e63c9
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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